How to convert long Word docs to .pdf docs?

[Saint 112]

Hi all

My environment is:

• MacBook Air M1.
• MacOS Ventura 13.6.1
• Word 2019

My Word files are basically text documents (they are essays) with some images but with nothing sophisticated in terms of layout. I don't do desktop publishing. The essay I need to convert has almost 600 pages with dozens of chapters and headers, a table of content, cross-references, URLs, etc.

I need to create a .pdf doc including those specs:

1. Internal links from table of contents to corresponding headers.
2. Cross-references.
3. URLs and mail addresses.
4. Maybe a couple of other features that I can't think of for the time being.

The PDF export in the Print box doesn't work for items #1 and 2 but works for item #3.

In Word the Save as PDF feature has some drawbacks:

• I made sucessful tests with a short document that includes chapters, a table of content, cross-references, etc. Once the PDF is opened in Preview everything works fine.
• But Word chokes with my big big essay. It just says "Can't export file. Something went wrong and your file can't be exported now. Please try again later." Of course it doesn't say what went wrong and why. I tend to think it has a size limit. It seems to be a common issue. I checked the RAM pressure in Activity Monitor: it's less than 50%.

I found the thread Word to PDF "Export failed due to an unexpected error" message in the Community forum and tried the work-around that is given to no avail. Moreover, when I copy or drag-and-drop the text from one document to a new file, parts of the text are in bold characters: it can be just a word here and there, parts of sentences, complete sentences, paragraphs, etc. It makes the work-around unusable.

Is there another trick to do the job?

I probably need a third party soft. It doesn't need to be very sophisticated. Do you recommend one? Free or affordable would be a plus.

BTW I looked for a user guide for Word and found only ones for the basics. Where a complete guide can be found? The Help tool is absolutely useless.

TIA

Regard

Nick

 

[MarshallG]

So… I assume you know how to use Styles to create headings and that you’re generating a table of contents using that, correct?



Given that, it sounds like 600 pages is just too much for Word. I’d first try rebooting the computer and running Word as the only application, but it will probably still fail.



The next thing I’d try is Adobe Acrobat. I think the one you want is Acrobat Distiller, but maybe just Acrobat (not the Reader version though). As I recall, Acrobat creates PDF’s and Distiller is a plug-in that lets other apps create PDF’s. So I’d just go with the standalone app. I think you can get a 30-day trial for free, or maybe your school gives you a free or discounted option. Once you generate it, proofread it, because there could be glitches in the middle of a document so large.




Large Word files can become corrupted in various ways. It can be maddening to track down the bad spot in your file. But let’s hope Acrobat solves your problem.

 

[CAcreeks]

Bummer, I thought Microsoft had fixed the long-document issues well before 2019. In the late 1990s, page limit was around 60 to 80. That's why organizations used FrameMaker instead of Word for technical documentation.

Have you tried MacOS Pages?

There's also TeX or LaTeX, but I don't see it (as such) amongst the Homebrew formulae.

In your web searches, have you found any indication that W10 can handle long documents better than Word on MacOS?

P.S. for MarshallG: doesn't Adobe Distiller require PostScript to produce PDF?

 

[hsphsp]

Just a suggestion that you try LibreOffice (LO) software. LO is a free opensource sw that can read word files and has a direct option for PDF. Of course, LO may not be able to handle such a large file any better, but it doesn't cost anything to try it.

 

[Saint 112]

Thanks for your quick response.

So… I assume you know how to use Styles to create headings and that you’re generating a table of contents using that, correct?

Right, of course, otherwise I wouldn't have a table of content.

I had asked the same question in the Microsoft Community : How to convert long Word docs to .pdf docs? (Word for Mac).

The moderator asked me: "When you use File>Save As>PDF, Word gives you a choice of Best for electronic distribution and Best for printing. Which of those have you tried?"

I had chosen the first (that's what my document is meant for) so I tried the second and voilà: it worked just fine and beyond my expectations!

Problem solved.

No need for a third party soft. They are damn expensive.

 

[Saint 112]

Thanks for your quick response. Check the preceding post: the problem is solved in an unexpected way.

Bummer, I thought Microsoft had fixed the long-document issues well before 2019. In the late 1990s, page limit was around 60 to 80. That's why organizations used FrameMaker instead of Word for technical documentation.

I started using Word (after using MacWrite ;-) ) in the early 90's and never had issues with document length.

Have you tried MacOS Pages?

I didn't think about it. I don't know recent versions. Formerly it would mess with Word's stuff like chapters, table of content, footnotes, etc.

Nick

 

[Saint 112]

Thanks for your quick response. Check the preceding post: the problem is solved in an unexpected way.

Just a suggestion that you try LibreOffice (LO) software. LO is a free opensource sw that can read word files and has a direct option for PDF. Of course, LO may not be able to handle such a large file any better, but it doesn't cost anything to try it.

I tried LO. Check the thread I had on the Microsoft Community : How to convert long Word docs to .pdf docs? (Word for Mac).

As a document it's unusable. Yet, to my surprise, the conversion was extremely fast.

Nick

 

[CAcreeks]

Thanks for your quick response.

So… I assume you know how to use Styles to create headings and that you’re generating a table of contents using that, correct?

Right, of course, otherwise I wouldn't have a table of content.

I had asked the same question in the Microsoft Community : How to convert long Word docs to .pdf docs? (Word for Mac).

The moderator asked me: "When you use File>Save As>PDF, Word gives you a choice of Best for electronic distribution and Best for printing. Which of those have you tried?"

I had chosen the first (that's what my document is meant for) so I tried the second and voilà: it worked just fine and beyond my expectations!

What I don't understand is how MacOS could have a "somewhat lame PDF algorithm" (in the words of the Microsoft forum responder) for electronic distribution, but not for printing. Seems like it would be the same algorithm.

When it comes to lame, nothing beats Word's HTML output for lameness.

Problem solved. No need for a third party soft. They are damn expensive.

I agree, Acrobat Pro is overpriced. Practically all software produces good PDF nowadays. The MacOS Preview program seems fine for commenting.

 

[Saint 112]

The moderator asked me: "When you use File>Save As>PDF, Word gives you a choice of Best for electronic distribution and Best for printing. Which of those have you tried?"

I had chosen the first (that's what my document is meant for) so I tried the second and voilà: it worked just fine and beyond my expectations!

What I don't understand is how MacOS could have a "somewhat lame PDF algorithm" (in the words of the Microsoft forum responder) for electronic distribution, but not for printing. Seems like it would be the same algorithm.

I was surprised by this statement too:

The PDF conversion feature that's included in the Print box apparently does just the same process as the job to send the data to the printer: links, cross-references, and so on are not needed so they are discarded. I use this feature very often. It serves perfectly its purpose, a simple one.

OTOH Word's PDF conversion feature has a bug in the Best for electronic distribution option. I am not the only one with the problem. It cannot handle long documents whereas the Best for printing option does the job not only perfectly well but in a jiffy, with the links even though they are useless for printing.

When it comes to lame, nothing beats Word's HTML output for lameness.

I never used this feature.

Problem solved. No need for a third party soft. They are damn expensive.

I agree, Acrobat Pro is overpriced. Practically all software produces good PDF nowadays. The MacOS Preview program seems fine for commenting.

All these softs are pro tools to produce sophisticated documents.

My need is just to export existing Word documents into pdf format with all its features. Once it's done I don't need to work on them.

BTW: for another purpose I need to create documents with user-editable fields. I tried in Word, LibreOffice and Pages by creating editable text boxes. But once it's exported into pdf the boxes are not editable anymore. Do you know of a simple way to do that?

 

[CAcreeks]

BTW: for another purpose I need to create documents with user-editable fields. I tried in Word, LibreOffice and Pages by creating editable text boxes. But once it's exported into pdf the boxes are not editable anymore. Do you know of a simple way to do that?

I believe you can do this with the Preview program.

Fill out and sign PDF forms in Preview on Mac

In Preview on your Mac, you can add text or a signature to a PDF form.

support.apple.com

 

[Saint 112]

BTW: for another purpose I need to create documents with user-editable fields. I tried in Word, LibreOffice and Pages by creating editable text boxes. But once it's exported into pdf the boxes are not editable anymore. Do you know of a simple way to do that?

I believe you can do this with the Preview program.

https://support.apple.com/lt-lt/guide/preview/prvw35725/mac

I used this feature but the issue is that the user can do whatever s/he wants with the editable fields: move them, delete them, resize them, etc. I want to create forms where the user can only fill the fields and do nothing else.